Abstract:
The influence of such Lewis acids as Et2O·BF3, ZnCl2, SnCl4 and TiCl4 on the stereochemical course of the Diels-Alder cycloadditions of sugar-derived (2S)-alkoxydihydropyranones was studied. The first two catalysts promoted the addition of dienes to give (3S,4aR,8aS)-3-alkoxy-4a,5,8,8a-tetrahydro-2-benzopyran-4-ones, and their concentration had almost no effect on the stereochemistry of the reaction. In contrast, the concentration of SnCl4 and TiCl4 had a remarkable influence on the selectivity, and even facial stereoselection reversal has been observed. These results may be ascribed to chelate complexation of the Lewis acid with the carbonyl and the vicinal alkoxy group of the dihydropyranone. © 2003 Elsevier Science Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones |
Autor: | Iriarte Capaccio, C.A.; Varela, O. |
Filiación: | CIHIDECAR-CONICET, Depto. de Quím. Orgán., Pabellón II, 1428 Buenos Aires, Argentina
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Palabras clave: | alkadiene; carbohydrate derivative; chelate; Lewis acid; pyran derivative; tin derivative; titanium derivative; zinc derivative; article; catalyst; chemical reaction; concentration (parameters); cycloaddition; Diels Alder reaction; proton nuclear magnetic resonance; stereochemistry; Betulaceae |
Año: | 2003
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Volumen: | 44
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Número: | 21
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Página de inicio: | 4023
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Página de fin: | 4026
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DOI: |
http://dx.doi.org/10.1016/S0040-4039(03)00851-7 |
Título revista: | Tetrahedron Letters
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Título revista abreviado: | Tetrahedron Lett.
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ISSN: | 00404039
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CODEN: | TELEA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v44_n21_p4023_IriarteCapaccio |
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Citas:
---------- APA ----------
Iriarte Capaccio, C.A. & Varela, O.
(2003)
. Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones. Tetrahedron Letters, 44(21), 4023-4026.
http://dx.doi.org/10.1016/S0040-4039(03)00851-7---------- CHICAGO ----------
Iriarte Capaccio, C.A., Varela, O.
"Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones"
. Tetrahedron Letters 44, no. 21
(2003) : 4023-4026.
http://dx.doi.org/10.1016/S0040-4039(03)00851-7---------- MLA ----------
Iriarte Capaccio, C.A., Varela, O.
"Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones"
. Tetrahedron Letters, vol. 44, no. 21, 2003, pp. 4023-4026.
http://dx.doi.org/10.1016/S0040-4039(03)00851-7---------- VANCOUVER ----------
Iriarte Capaccio, C.A., Varela, O. Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones. Tetrahedron Lett. 2003;44(21):4023-4026.
http://dx.doi.org/10.1016/S0040-4039(03)00851-7